Hydrochloric Acid → HCID 66976007, compound

To a suspension of calcium chloride (27.6 g) in THF (234 mL) and ethanol (176 mL) was added, under a nitrogen stream, sodium borohydride (12.5 g), and the mixture was stirred at room temperature for 1 hr. To the reaction mixture was added a solution of methyl (2RS,3RS)-2-[(benzylamino)methyl]-3-(4-chloro-3-fluorophenyl)-3-hydroxypropanoate (58.2 g) in THF (200 mL) and ethanol (150 mL) under ice-cooling, and the mixture was stirred at room temperature for 5 hr. To the reaction mixture was added 6 N aqueous hydrochloric acid solution (28 ml), the mixture was neutralized with 8 N aqueous sodium hydroxide solution, and the mixture was filtered through celite. The obtained oil was diluted with ethyl acetate, and the diluted solution was washed with distilled water and brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give the title compound (44.5 g).

1. temperaturecooling
2. stirringthe mixture was stirred at room temperature for 5 hr
3. filtrationthe mixture was filtered through celite
4. additionThe obtained oil was diluted with ethyl acetate
5. washthe diluted solution was washed with distilled water and brine
6. dry with materialdried over anhydrous sodium sulfate
7. concentrationconcentrated under reduced pressure

ORD record

ord-8316f730db7a4f0ba1c68a3e40009e64

Source dataset

uspto-grants-2014_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08722662B2